Benzaldehyde, 4-hydroxy-3-methoxy-2-nitro- → HCID 136397840, compound

HRID 47267Notes

Reaction equation

HRID 47267 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[C:4]([N+:10]([O-:12])=[O:11])[C:3]=1[O:13][CH3:14].[NH:15]([C:17]1[CH:22]=[CH:21][C:20]([C:23]2[C@H:24]([CH3:30])[CH2:25][C:26](=[O:29])[NH:27][N:28]=2)=[CH:19][CH:18]=1)[NH2:16]>C(O)C>[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[N:16][NH:15][C:17]2[CH:22]=[CH:21][C:20]([C:23]3[C@H:24]([CH3:30])[CH2:25][C:26](=[O:29])[NH:27][N:28]=3)=[CH:19][CH:18]=2)=[C:4]([N+:10]([O-:12])=[O:11])[C:3]=1[O:13][CH3:14]

Participants

4

Reactant 2

HCID 96959Benzaldehyde, 4-hydroxy-3-methoxy-2-nitro-HCID 69529174(R)-6-(4-hydrazino-phenyl)-5-methyl-4,5-dihydro-2H-pyridazin-3-one

Product 1

HCID 136397840HCID 136397840, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 4-hydroxy-3-methoxy-2-nitro-benzaldehyde (1.6 g) in ethanol (15 ml) was added to a suspension of (R)-6-(4-hydrazino-phenyl)-5-methyl-4,5-dihydro-2H-pyridazin-3-one (1.75 g) in ethanol (20 ml) and the resulting mixture refluxed for two hours. The resulting crystals were filtered at room temperature and washed with ethanol. Yield 2.37 g. HPLC: purity 99.4%, optical purity 99.8%.

Workup

  1. temperaturethe resulting mixture refluxed for two hours
  2. filtrationThe resulting crystals were filtered at room temperature
  3. washwashed with ethanol

Sources & evidence

ORD record
ord-b9d0cf976a794ddeb6ba1b5f4e6d51f5
Source dataset
uspto-grants-2004_03
Patent number
US06699868B2

Reaction notes

Loading…